proline dl-form → 5-[(2-Bromo-1,3-thiazol-5-yl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 561388

反応式

HRID 561388 の反応式
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.N1CCCC1C(O)=O.[Br:19][C:20]1[S:21][C:22]([CH:25]=O)=[CH:23][N:24]=1.[CH3:27][S:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:38]=1[NH:37][CH:36]=[CH:35]2>C(#N)C>[Br:19][C:20]1[S:21][C:22]([CH:25]([C:35]2[C:34]3[C:38](=[C:30]([CH2:29][S:28][CH3:27])[CH:31]=[CH:32][CH:33]=3)[NH:37][CH:36]=2)[CH:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])=[CH:23][N:24]=1

参加物

6

反応物 4

HCID 614proline dl-formHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27732592-Bromo-1,3-thiazole-5-carbaldehydeHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

生成物 1

HCID 583922715-[(2-Bromo-1,3-thiazol-5-yl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1.02 g (7.08 mmol) of Meldrum's acid, 0.04 g (0.34 mmol) of D,L-proline and 1.36 g (7.08 mmol) of 2-bromo-5-formylthiazole were successively added to a solution of 1.30 g (6.75 mmol) of the compound from Example 8A in 50 ml of acetonitrile. The reaction mixture was stirred at RT overnight and then the solvent was removed in vacuo. Purification of the residue by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5) resulted in 3.58 g (81% purity, 87% of theory) of the title compound.

後処理

  1. customthe solvent was removed in vacuo
  2. customPurification of the residue by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5)

出典と根拠

ORDレコード
ord-f7633072c4254390973e72a6a89551ba
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

関連ノート

読み込み中…